title: L-Proline catalyzed reaction of N-confused porphyrin and active methylene compounds.
abstract: Active methylene compounds such as acetone, butanone, cyclopentanone, nitromethane, malononitrile, ethyl 2-cyanoacetate, diethyl malonate, and ethyl acetylacetate react with the C3 position of N-confused porphyrin in the presence of L-proline in refluxing THF-EtOH affording a variety of N-confused porphyrin derivatives in moderate yield. L-Proline catalyzes the reaction facilitating the formation of the carbanion derived from an active methylene compound simultaneously delivering protons to the N-confused porphyrin. Both processes are key factors of this reaction.
authors.affiliation: Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201, China.
authors.forename: Bin
authors.initials: B
authors.lastname: Liu
authors.forename: Xiaofang
authors.initials: X
authors.lastname: Li
authors.forename: Jie
authors.initials: J
authors.lastname: Zhang
authors.forename: Piotr J
authors.initials: PJ
authors.lastname: Chmielewski
mesh_terms: D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry*
chemical_list: D011166:Porphyrins; D011392:Proline